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EP0490176B1 - Catalyseurs polyuréthane - Google Patents

Catalyseurs polyuréthane Download PDF

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Publication number
EP0490176B1
EP0490176B1 EP91120352A EP91120352A EP0490176B1 EP 0490176 B1 EP0490176 B1 EP 0490176B1 EP 91120352 A EP91120352 A EP 91120352A EP 91120352 A EP91120352 A EP 91120352A EP 0490176 B1 EP0490176 B1 EP 0490176B1
Authority
EP
European Patent Office
Prior art keywords
amino
acid
catalysts
tin
theory
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP91120352A
Other languages
German (de)
English (en)
Other versions
EP0490176A2 (fr
EP0490176A3 (en
Inventor
Volker Dr. Ullrich
Clemens Dr. Schudok
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhein Chemie Rheinau GmbH
Original Assignee
Rhein Chemie Rheinau GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhein Chemie Rheinau GmbH filed Critical Rhein Chemie Rheinau GmbH
Publication of EP0490176A2 publication Critical patent/EP0490176A2/fr
Publication of EP0490176A3 publication Critical patent/EP0490176A3/de
Application granted granted Critical
Publication of EP0490176B1 publication Critical patent/EP0490176B1/fr
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Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds

Definitions

  • the invention relates to catalysts for the production of solid and foamed polyurethanes.
  • polyurethanes PUR
  • various classes of substances are known as catalysts for activating the reaction of isocyanates with polyols and / or the reaction of isocyanates with water, e.g. Amines (cyclic, acyclic; monoamines, diamines, oligomers with one or more amino groups) and organometallic compounds, primarily those of tin, iron, bismuth and mercury (see Kunststoff-Handbuch, Vol. 7, pp. 92-99, Karl- Hanser Verlag, Kunststoff (1983)).
  • Amines cyclic, acyclic; monoamines, diamines, oligomers with one or more amino groups
  • organometallic compounds primarily those of tin, iron, bismuth and mercury
  • the invention relates to migration-resistant and odorless catalysts for the production of polyurethanes and a process for their production.
  • reaction products are crystalline, odorless and clearly soluble in polyether polyols, polyester polyols and in the usual glycols such as ethylene glycol and dipropylene glycol.
  • the preparation of the catalysts can be done by the general reaction equation to be discribed.
  • Dibutyltin oxide is reacted with 2-3 moles of the corresponding aminocarboxylic acid, preferably with 2-2.5 moles, in an inert solvent.
  • the water formed is distilled off azeotropically.
  • amino carboxylic acids 3,5-diaminobenzoic acid, 4-amino-2-hydroxybenzoic acid, 2-amino-3-hydroxybenzoic acid, 2-aminobenzoic acid, 3-amino-2-hydroxybenzoic acid, 5-amino-2-hydroxybenzoic acid, 2-amino -4-hydroxybenzoic acid, 2-amino-5-hydroxybenzoic acid, 3,4-diaminobenzoic acid, 4-amino-3-methylbenzoic acid, 2-amino-6-methylbenzoic acid, 2-amino-3-methylbenzoic acid, 2-amino-5-methylbenzoic acid , 2-amino-5-chlorobenzoic acid, 3-amino-4-chlorobenzoic acid, 4-amino-2-chlorobenzoic acid, 5-amino-2-chlorobenzoic acid, 2-amino-3-octylbenzoic acid, 2-amino-3-hexylbenzoic acid.
  • Dlbutyltin oxide is reacted with about 2 moles of the corresponding aromatic aminocarboxylic acid in substance with azeotropic distillation of water to give the corresponding tin dicarboxylate.
  • these catalysts are e.g. Dibutyltin dilaurate and dibutyltin diacetate are not susceptible to hydrolysis.
  • Polyol formulations which may contain water, catalysts, optionally stabilizers, paints, flame retardants or other fillers, are stable on storage using the catalysts described, without losing their reactivity.
  • the catalysts can be used in an amount of from 0.01 to 1% by weight, in particular from 0.1 to 0.6% by weight, based on the polyol.
  • the components polyol, filler and catalyst are mixed homogeneously at 20 ° C.
  • the time until the PU system has fully cured is measured in a homogeneous mixture of component A and component B (pot life).
  • the storage stability of a catalyst is checked by storing component A containing the catalyst at 60 ° C. in a sealed container and determining the change in the pot life over the storage time.
  • the components polyol, water and catalyst are mixed homogeneously at 20 ° C.
  • the time until the PU foam system has fully hardened is measured in a homogeneous mixture of components A and B (adhesive free time).
  • the hydrolytic stability of an activator is checked by storing component A containing the catalyst at 25 ° C. in a sealed container and measuring the extension of the tack-free time at certain intervals.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Claims (3)

  1. Produits réactionnels de 1 mol d'oxyde de dibutylétain et de 2 mol d'acide 2-aminobenzoïque ou d'un acide aminocarboxylique aromatique de formule :
    Figure imgb0008
     dans laquelle
    R₁ et R₂ représentent chacun indépendamment -OH, Cl, -NH₂, -(CH₂)n-CH₃ (n = 1-6) et R₂ représente de plus H.
  2. Utilisation des produits réactionneis selon la revendication 1 en tant que catalyseurs pour la production de polyuréthanes.
  3. Procédé de production des produits réactionnels selon la revendication 1, caractérisé en ce qu'on fait réagir 2 mol d'acide 2-aminobenzoïque ou d'un acide aminocarboxylique de formule (I) et 1 mol d'oxyde de dibutylétain avec une distillation azéotrope de l'eau formée.
EP91120352A 1990-12-11 1991-11-28 Catalyseurs polyuréthane Expired - Lifetime EP0490176B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4039448 1990-12-11
DE4039448A DE4039448A1 (de) 1990-12-11 1990-12-11 Polyurethan-katalysatoren

Publications (3)

Publication Number Publication Date
EP0490176A2 EP0490176A2 (fr) 1992-06-17
EP0490176A3 EP0490176A3 (en) 1992-08-26
EP0490176B1 true EP0490176B1 (fr) 1995-10-11

Family

ID=6420022

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91120352A Expired - Lifetime EP0490176B1 (fr) 1990-12-11 1991-11-28 Catalyseurs polyuréthane

Country Status (4)

Country Link
US (1) US5155248A (fr)
EP (1) EP0490176B1 (fr)
DE (2) DE4039448A1 (fr)
ES (1) ES2077774T3 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6020283A (en) * 1998-12-02 2000-02-01 Bayer Corporation Process for the production of delayed action tin catalysts
US6140381A (en) * 1998-12-02 2000-10-31 Bayer Corporation Delayed action catalysts for carpet backing and air frothed foam
CN1073572C (zh) * 1999-06-02 2001-10-24 山西大学 单核二酰异羟肟酸类二烃基锡化合物及其合成
CN1073570C (zh) * 1999-06-02 2001-10-24 山西大学 单核杂环羧酸类二丁基锡化合物及其合成
CN1073568C (zh) * 1999-06-02 2001-10-24 山西大学 二配体双核二酰异羟肟酸类二烃基锡化合物及其合成
CN1073566C (zh) * 1999-06-02 2001-10-24 山西大学 双核芳香族、杂环类单酰异羟肟酸二烃基锡化合物及其合成
CN1073567C (zh) * 1999-06-02 2001-10-24 山西大学 三配体双核二酰异羟肟酸类二烃基锡化合物及其合成
CN1073571C (zh) * 1999-06-02 2001-10-24 山西大学 单核芳香族、杂环类单酰异羟肟酸二烃基锡化合物及其合成
CN1073569C (zh) * 1999-06-02 2001-10-24 山西大学 多核杂环羧酸类二丁基锡化合物及其合成
US9856214B2 (en) 2013-11-15 2018-01-02 The Wistar Institute Of Anatomy And Biology EBNA1 inhibitors and their method of use
JP6771491B2 (ja) 2015-05-14 2020-10-21 ザ ウィスター インスティテュート オブ アナトミー アンド バイオロジー Ｅｂｎａ１阻害剤およびその使用方法
TW201946919A (zh) 2018-05-17 2019-12-16 威斯塔研究所 Ebna1抑制劑晶形、其製備方法及其使用方法
CN109971180A (zh) * 2019-02-25 2019-07-05 袁玲燕 一种高耐温导热硅脂及其制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3509104A (en) * 1967-03-01 1970-04-28 Ferro Corp Dialkyltin salt of aromatic carboxylic acids useful as catalysts in producing urethanes and polyurethanes
US3622524A (en) * 1968-09-03 1971-11-23 Gen Electric Compositions of epoxy resins cured with organotin compounds
US3922253A (en) * 1971-10-28 1975-11-25 Ppg Industries Inc Self-crosslinking cationic electrodepositable compositions
US4028313A (en) * 1975-06-25 1977-06-07 Bayer Aktiengesellschaft Process for the production of water-dispersible polyhydroxyl compounds
DE3044106A1 (de) * 1979-11-30 1981-09-03 Yoshitomi Pharmaceutical Industries, Ltd., Osaka Verfahren zur herstellung von polyurethanen
US4360670A (en) * 1981-02-02 1982-11-23 Air Products And Chemicals, Inc. Amino and amido dialkyl tin carboxylates
US4816593A (en) * 1987-12-21 1989-03-28 Cardinal Reserach & Development Co., Inc. Heterocyclic organotin compounds
US4987244A (en) * 1989-09-11 1991-01-22 Air Products And Chemicals, Inc. Organotin catalysts for use in polyurethane systems
US5089645A (en) * 1989-09-11 1992-02-18 Air Products And Chemicals, Inc. Hydroxyl-containing organotin catalysts for making polyurethanes

Also Published As

Publication number Publication date
ES2077774T3 (es) 1995-12-01
DE59106677D1 (de) 1995-11-16
EP0490176A2 (fr) 1992-06-17
US5155248A (en) 1992-10-13
EP0490176A3 (en) 1992-08-26
DE4039448A1 (de) 1992-06-17

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